Joan Holloway: [to Peggy] You want to be taken seriously? Stop dressing like a little girl.

Joan Holloway: [to Roger] One day you'll lose someone who's important to you. You'll see. It's very painful.

Joan Holloway: He may act like he wants a secretary, but most of the time they're looking for something between a mother and a waitress. And the rest of the time, well... Go home, take a paper bag and cut some eye holes out of it. Put if over your head, look in the mirror and try and evaluate your strengths and weaknesses. And try and be honest.

Joan Holloway: Peggy, this isn't China. There's no money in virginity.

Joan Holloway: Roger, if you had your way, I would be stranded in some paperweight with my legs stuck in the air.

John Hooker: Mr. Kinsey, you might want to shave your beard.
Paul Kinsey: What? Who the hell are you people?
John Hooker: That was a joke.

Ken Cosgrove: New York in August? It's like a great big hairy armpit museum.

Ken Cosgrove: Still working Campbell? There's no reason to show off... Cooper's in Montana, Sterling's in Jane and Draper's on vacation.

Ken Cosgrove: [after Joan bends over in front of the 2-way mirror] I wanna stand and salute that.

Lane Pryce: Mr. Hooker! I've been sacked. Please have my office and things put in storage at this address.
John Hooker: What's happened?
Lane Pryce: You're a sharp boy, you'll figure it out.

Lane Pryce: So we finally have an answer to the question 'What makes Don Draper smile?' Five thousand dollars seems to be the number.

Lane Pryce: What about our other clients?
Roger Sterling: We have no other clients! If Lee Garner, Jr. wants three wise men flown in from Jerusalem, he gets it.

Midge Daniels: [to Don on the phone as Peggy listens] I want you to pull my hair and ravish me and leave me for dead.

Midge's Friend: Dig. Ad man's got a heart.
Midge Daniels: The grown-ups are talking.
Midge's Friend: Don't defend him. [to Don] Toothpaste doesn't solve anything. Dacron sure as hell won't bring back those ten dead kids in Biloxi.
Don Draper: Neither will buying some Tokaj wine and leaning up against a wall in Grand Central pretending you're a vagrant.
Midge's Friend: You know what it's like to watch all you ants go into your hive? I wipe my ass with the Wall Street Journal.
Woman: How come every time we have a party the ladies have to sit and listen to the men talk?
Midge's Friend: Look at you. Satisfied, dreaming up jingles for soap flakes and spot remover, telling yourself you're free.
Don Draper: Oh, my God. Stop talking and make something of yourself.
Roy: Like you? You make the lie. You invent want. You're for them... not us.
Don Draper: Well, I hate to break it to you, but there is no big lie. There is no system. The universe is indifferent.

Paul Kinsey: [after smoking marijuana] If you were feeling it, you'd be hungry.
Peggy Olson: I am hungry. It's just not worth moving.